1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 1220696-34-3
• Molecular Formula: C14H19BN2O2
• Molecular Weight: 258.12386
• Mol file: 1220696-34-3.mol

Synonyms:1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Chemical Property of 1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• PSA: 36.28000
• LogP: 1.87250
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

There total 4 articles about 1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (754214-56-7) + methyl iodide (74-88-4) → (S)-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1220696-34-3)

Guidance literature:

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

Reference yield:

bis(pinacol)diborane (73183-34-3) + 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (183208-22-2) → (S)-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1220696-34-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 8h; Inert atmosphere;

Reference yield:

5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7) → (S)-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1220696-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 3 h / 25 °C / Inert atmosphere

2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 8 h / 90 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium hydride; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

methyl iodide

bis(pinacol)diborane

5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Downstream raw materials:

2-((trans-4-hydroxycyclohexyl)amino)-4-(3-isopropyl-4-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile